Yes, Tupac was wearing this year's faded-denim look back in '93. But his enduring influence on fashion lies in the confrontational attitude—his energy gave his clothes a whole different context

Photo: Reuters/Pool/London

2/7

HIM AGAINST THE WORLD

Nobody flouted authority like Pac. This is what he wore to court in 1994 to face a weapons charge.

Photo: Courtesy of Eric Wise/ Conde Nast Archive

3/7

EVEN HIS CLOTHES HAD TATTOOS

To Tupac, "Thug Life" was a revolutionary code that he hoped would become a movement. So he went to the tattoo parlor and splashed it across his clothes—a branding strategy that's stronger than ever in hip-hop now.

Photo: LFI/ Photoshot

4/7

HIP-HOP'S ORIGINAL COSMOPOLITAN

Tupac was the first rapper to move seamlessly between Hollywood and the fashion world. (He supposedly even had a fling with Madonna.) His style was diverse, but he wasn't a chameleon. No matter where his talent took him, the chains and bandannas remained.

Photo: Dorothy Low/ Shooting Star

5/7

HE GOT AROUND

Athletic wear and Air Jordans are once again the pinnacle of style. (You'll just want your track suit to fit a little snugger than Pac's.)

Photo: Mike Miller

6/7

LIL WAYNE OWES HIM ROYALTIES

All due respect to Weezy, Rick Ross, and the entire NBA, but Pac got tatted up first. His Thug Life piece is hall-of-fame material.

Photo: Mike Miller

7/7

DID YOU GET THE MEMO?

Back in '94, a young black man with tattoos and a big diamond watch was already an eff you to America. But Pac always added the finger, too, just in case.

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